The Why Threshold

Freedom through alignment.

Jul 16, 2025

A Simple Tool

I have this concept I call the Why Threshold. It’s a self-awareness tool I use to decide where to focus my time and energy. A Why Threshold marks the point where my curiosity to keep asking “why” fades—a signal that I’ve reached my natural limit of interest or utility in a subject. Recognizing this threshold has helped me align my pursuits with my true interests and better understand the motivations of others, especially in collaborative settings.

The general concept is straightforward: When exploring something new, whether in a novel field or one in which you’re already well-versed, take note when your curiosity to answer the next why wanes. This is a reliable early sign that you’re at or near your Why Threshold, the place where you’ve learned as much as you’re naturally inclined and the utility of pushing further relative to your needs has diminished. False signals can arise from fatigue or over-exposure, but if the desire to answer the next why doesn’t return after giving yourself some distance from the work, you’ve likely reached your Why Threshold.

We each have our own distinct Why Thresholds for everything in our lives. Often inexplicably, we’re drawn towards certain subjects or activities yet have little to no interest in others. Our Why Thresholds for the things we’re interested in are higher than for those we’re not, and when we never reach our Why Threshold for a certain subject or activity, it’s a good sign our actions and interests are in very strong alignment.

The opposite is also true, and respecting our Why Thresholds helps us to avoid needlessly pushing ourselves too far. Burnout happens beyond our Why Thresholds as does a drop-off in productivity and the quality of our decision-making.

Working alongside others whose Why Thresholds are aligned with our own makes collaboration smoother and more fruitful. When this is not the case, imbalances emerge that can reveal the misplacement of resources. Becoming sensitive to the Why Thresholds of those with whom you work can teach you more about your colleagues than simply trying to determine whether or not they like their work or the degree to which they care about it.

It’s for these reasons that I’ve come to rely heavily on my Why Thresholds for feedback about how I spend my time and with whom I spend it. Before I get further into the details, I’d like to first share how the concept of the Why Threshold came to me.

While Building A Fence

The first person who really sparked my interest in trading as a career was an independent trader I met through a “regular” at one of my restaurants. He is a personal trainer, Crossfit enthusiast, Arsenal FC fan, PhD in economics, and volatility market specialist. Quite the combo. I was lucky enough to have a few opportunities to pick his brain in person and over email, but most of what I learned from him was on Twitter/X.

Once you follow one “VOL” person on X, the algo points you to many of the others. I was soon studying everything Benn Eifert, Cem Karsan, Kris Sidial, Noel Smith,

Jim Carroll

, Vance Harwood,

Kris Abdelmessih

, and many others shared. To get fully immersed, I decided to read volatility and options books by Hari Krishnan and Euan Sinclair. I was overwhelmed, intimidated, and felt supremely inadequate.

During the early information gathering stage of my trading journey, there were plenty of times when I encountered math and topics far beyond my understanding, but even in those instances I was often able to pick up an important insight from the context. And just as importantly, these guys (yes, they’re all men) helped lift the veil on how markets actually work. It was fascinating, and at every turn I found myself asking why, wanting to know more. But then one day something changed.

I don’t remember who it was, but during a podcast interview one of the aforementioned PhDs went deep on one of his options models, and I wasn’t able to follow along. This made me feel insecure and like an imposter. What changed this time was that I didn’t feel an impulse to try to figure out what the interviewee was talking about. I was no longer interested in asking or answering this next why.

It took me by surprise. At first, I thought my subconscious was throwing in the towel. “If you aren’t willing to keep pushing, it’s time to walk away and find another path.” Earlier in my days of trading I thought I was going to need to get a Masters and possibly a Doctorate to be worthy of trading options. But then this happened, and what came shortly thereafter was a sense of calm and relief.

I didn’t need to go back to school. I didn’t need to get a job at a bank or at a hedge fund. I didn’t need to be able to write code for a proprietary trading algorithm or create a new options pricing model. And not only did I not need to do those things, it was OK that I had no interest in going that deep.

I was building a fence on my property when these thoughts flooded in, and as I made my way back to the house, the whole concept of the Why Threshold came to me. After years of wanting to answer why, I’d finally hit my threshold, and now I was free to move on.

Alignment Within a Group

When my business partners and I opened our second restaurant, I made sure to have employees from the existing restaurant on the new restaurant’s schedule every shift. My thinking was that these established employees would help me work out the systems of the new spot since they were already familiar with my operational framework, business preferences, and communication style. I also felt they’d help carry over our company culture into the new restaurant. These things played out as I’d hoped but something I hadn’t anticipated quickly emerged.

Some of the most obvious performance gaps between existing and new employees were amongst the support staff, i.e. food runners, bussers, and barbacks. These jobs are highly repetitive and the tasks are relatively simple, but they are far from mindless. As a baseline, for someone to be competent in these roles they must have good situational awareness and they must be anticipatory machines. As much as the tasks themselves aren’t complicated and most anyone can physically do them, what I discovered was that the highest performers had figured out something else: the why.

To be proficient, one had to have good pattern recognition. To be great, one had to understand why the patterns even existed.

As an owner of a business, many of the whys are inherent to you or you seek them out naturally as you learn how to run your business. The business is yours and therefore so are the whys. For your employees, some of the whys will be observed, others can be taught, and still others must be discovered through experience. The employees who I brought into the second restaurant had worked alongside me oftentimes for years, absorbing the whys so deeply that they’d become their own. When dropped into the new business, the existing employees had a significant advantage because even though the whats, wheres, and hows had changed, the foundational whys had not.

When I look back now I can see that the employees who flourished and stayed with us for years had Why Thresholds that were aligned with the level of service and execution that we were trying to achieve as an organization. This certainly wasn’t the only factor, but if an employee’s desire to understand the whys pushed them far enough, it often resulted in superior performance and greater job satisfaction. With these staff members, it was obvious to everyone around them, co-workers and customers alike, that they were in the right place doing the right work.

Going a step further, amongst our employees, those whose Why Thresholds were aligned with one another’s preferred to work together and would seek out ways to collaborate on new initiatives. These collaborative endeavors generated opportunities for employees to be creative and take ownership over a project of their own while enhancing the customer experience and supporting the business. These efforts established trust between me and the employees, which led to an openness (freedom) to explore and expand their roles further within the company.

It was powerful to witness these dynamics in action within businesses with so many moving parts and personalities. At some point, a nucleus emerged of employees whose Why Thresholds aligned, and that was when our “culture” really took root and the businesses flourished.

Alignment Within Oneself

“Do what you love and you’ll never work a day in your life.”

“Follow your passion and the money will come.”

“If you’re passionate enough about what you do, success is inevitable.”

Catchy and inspirational but useless in practice, the underlying assumption in these cliches is that we know what are our passions are. As much as I’m a proponent of expanding our freedom through pursuing our life’s work, I also know self-discovery and fulfillment are ongoing processes, rarely revelatory events, with many false starts, frustrations, and setbacks along the way.

I’m a firm believer in the idea that life is very much a journey of addition through subtraction. At the end of this journey, our I Don’t Like To Do This list will be considerably longer than our I Like To Do This list. For most of us, it’s much easier to add things to the first list than the second, and that’s where the Why Threshold can help.

Like many of you I’m sure, I’ve stuck it out in many projects and jobs simply for the sake of finishing what I started even though the work had gone from stimulating and rewarding to tiresome and counterproductive. In the moment we may think we’ll only be free from the work when it’s finished completely. Yet the time we spend finishing the unessential steals more real freedom from us than the perceived freedom we think we’ll gain from slapping a bow on a fully completed task.

It’s worth considering that on this quest for greater freedom, robotically finishing everything we start or attempting to do more than we must is rarely the best practice. Using our Why Thresholds to inform us when a pursuit has run its course can save us a lot of angst and time. Similarly, when we bump into Why Thresholds early and often during a project, it’s likely a sign that you need to take out your I Don’t Like To Do This list and a sharp pencil.

Our Why Thresholds are signals from within telling us it’s time to consider making a choice. In his book Essentialism, Greg McKeown distills the entire practice of Essentialism down to choice. In his words, Essentialism is a “heightened sense of our ability to choose” and it “cannot be taken away or even given away - it can only be forgotten.”

So, how do we forget our ability to choose? I believe it happens as we intentionally tune out or unintentionally become desensitized to the internal signals that strive to keep us aligned with our innate interests and curiosities. Developing our sensitivity to our Why Thresholds is an effective way to keep these signals clear and eliminate the unessentials that eat up our time and erode our freedom.

Yeah, but…

There are absolutely times when something needs to be finished regardless of how we feel about it. Deciding whether to respect a Why Threshold or push past it can be difficult. An easy test is to determine whether the current task is a necessary component of a larger effort for which you have not yet reached your Why Threshold. If that’s the case, keep chugging. If it’s not, it may be time for a pivot.

It’s also important to acknowledge that growth can happen beyond our Why Thresholds, and sometimes the extra effort resets our Why Thresholds to a higher level or introduces us to a new subject in which there is greater interest. That’s why I don’t often abandon something at the first encounter with a Why Threshold; better to get some space from the work and come back to it later to see if interest has reemerged or if there’s an adjacent path you do want to explore.

Just because I came to peace with not needing a PhD to trade options didn’t mean I stopped exploring options completely. Rather than try to learn all the math underpinning options values, I pivoted and went deeper into what can be learned about the broader market from studying options markets as a whole. Many years later and I’ve yet to reach my Why Threshold on that subject.

The Ultimate Trade-Off

The concept of trade-offs is one I plan to explore more thoroughly in a future post, but at its core, a trade-off is a choice. The ultimate trade-off is between time and how we choose to spend it. If we believe our freedom can be expanded by allocating our time to efforts that bring us meaning and purpose (I do), then respecting our Why Thresholds is a powerful way to ensure our limited time and energy are deployed judiciously. In practice, I’ve found that combining my awareness of my Why Thresholds with an assessment of how I feel about an activity before I start it, while doing it, and after it is done, is an effective way to keep me on track.

For instance, if I feel anticipation ahead of starting a project or job and am curious about what I might learn, that’s a great first sign. While in the midst of the work, even if I find it challenging and frustrating, if it keeps me engaged and every why motivates me to push further, I know I’m on the right path. And once the work is complete, if I walk away feeling grateful for what I learned, proud of what I accomplished, and motivated to build on the experience, I know I traded my time wisely.

If you want to do away with the unessential and commit as much of your time as possible to the activities that resonate with your most fundamental interests, developing an awareness of and sensitivity to your Why Thresholds is an impactful way to do it. We are perpetually inundated with stimulus from the world around us telling us what we need, what we should do, and how we should live, but that noise is rarely anything but a distraction. The most important feedback, the real signals, come from within, and it’s our duty to listen to what those signals are saying and adjust our behavior accordingly. Our Why Thresholds can help us do exactly that.

As always, thank you for reading The Free Dominion. If there are any topics related to freedom that interest you, please let me know. I really would love for this to become a conversation.